


Crush

by thatwriterlady



Category: Supernatural
Genre: Castiel Has a Crush on Dean Winchester, Castiel/Dean Winchester First Kiss, Coming Out, Dean Winchester Has a Crush on Castiel, Dean Winchester and Feelings, Dean's a fantastic father, F/M, Fluff, John Winchester's A+ Parenting, Longing, M/M, Mention Of Homophobia, Mention of angst regarding coming out, Mutual Pining, Revelations, Single Parent Castiel, Single Parent Dean, Teacher Dean Winchester, Tiny amount of angst, Writer Castiel, You Know You WANT To, just read it already, so is Castiel
Language: English
Status: Completed
Published: 2015-12-30
Updated: 2015-12-30
Packaged: 2018-05-10 09:28:40
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 10,191
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5580310
Author URL: https://archiveofourown.org/users/thatwriterlady/pseuds/thatwriterlady
Summary: <blockquote class="userstuff">
              <p>1992- Dean had a crush on quiet, nerdy Cas Novak, but due to the time and where they lived he couldn't come out and tell the other boy he liked him.  He had no idea that anxious, introverted Cas liked him in return.  </p><p>Feelings were never revealed and both boys grew up, moved on, started their own lives, both certain they'll never again see one another.  </p><p>But what if fate has something else in store for them?</p>
            </blockquote>





	Crush

**Author's Note:**

> So I do hope you all enjoy this one. It was just an idea that came to me, so I had to write it. You know, OCD an all that.

**September 1992**

“I know you like him. Why won’t you just admit it?” Charlie was leaning back against the locker next to Dean’s and giving him her most exasperated look.

“Shut up! You know I can’t just come out! I’d be persecuted, and my dad would kill me. You know this. Liking someone doesn’t mean crap. I have another two years here in this shit hole. I’m not going to make it a living hell for me or for him.” Dean whispered the words, but there was a harshness to them that clearly told her he was serious. Almost as though the Gods in heaven were conspiring to torment him, the object of his affections chose that moment to walk by. Cas had his nose buried in a book, which was typical. His dark hair was messy and his glasses were sliding down his nose. Unconsciously he pushed them up, his blue eyes (something Dean loved to stare into) staying locked on the pages of his book as he passed by. Naturally Dean’s eyes followed the other boy’s passage. 

“Dean, you’ve got it bad, you know that?” Normally Charlie would joke around but right now she was being serious, and he could hear the pity in her voice. He hated being pitied. Turning back to his locker he grabbed out his biology and English books before slamming the door and stomping off. Charlie stayed where she was. She knew better than to follow when he was in a mood like that. Later she would check on him, after he had calmed down.

 

Cas jumped when he heard the locker slam, and he spun around to see Dean Winchester glaring at Charlie Bradbury. He moved over to the lockers closest to him, pressing himself between the lockers and the classroom door as he clutched his Patterson novel to his chest. He watched Dean storm off. When he turned back around he noticed Charlie was watching him. Ducking his head he hurried off before she could speak to him. It wasn’t that he didn’t like Charlie, because he did, she was friendly and bubbly. It was more that he was painfully shy and had difficulty talking to most people, even ones as nice as she was. As he hurried towards his Calculus class his thoughts turned back to Dean. He’d had a crush on the boy since first laying eyes on him freshman year, but it wasn’t socially acceptable for boys to date one another, not in Lawrence, Kansas. If he were living in California he would have tried to reach deep down inside himself to come up with the courage to tell Dean how he felt about him. Dean was the most amazing boy he’d ever seen in his life. He was gentle and thoughtful, and any time Cas happened to look in his direction, Dean always had a smile for him, and it always made Cas’ stomach do a flip. What made him hold back was knowing that to tell Dean how he felt was to not only make himself vulnerable but it had the potential to make Dean the laughing stock of the school, and he couldn’t submit Dean to that kind of torture either. That and the fear that Dean was straight and would be horrified to know that the geeky boy in the huge glasses and oversized sweaters had a crush on him. No, it was best to keep his crush to himself, for both of their safety. But mostly for his own.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

**September 2015**

“Dad, I got asked out today.” 

Dean slid his reading glasses off and looked up at his daughter. “Oh yeah? What’s his name?”

His daughter, Addison, sat down on the chair next to Dean and looked up at him with large, hazel eyes full of excitement.

“His name is Bill and he’s in my English and History classes, and he’s in the GSA with me. That’s where we met. I have been crushing on him since freshman year; he’s gorgeous and so sweet!” She was practically bouncing in her seat. He chuckled and set aside the papers he’d been reviewing to focus on her.

“GSA? Is he an ally or…?” He didn’t want to make any assumptions.

“Oh, he’s an ally. His dad is gay. Bill’s going to take me out this Friday.” 

Dean smiled at her excitement. This was only the second boy that had asked her out, and he was happy for her. Sure, he worried, but he was happy for her.

“He’s coming to pick you up, right?”

“Yep, and you can meet him then,” she said happily.

“Alright. Go do your homework, dinner will be ready at six.” He watched as she got up, bouncing her way out of the kitchen. Shaking his head, he chuckled. She was growing up much too fast.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~

When Friday came Dean was busy unwrapping a frozen pizza for himself when the doorbell rang. He balled up the plastic and tossed it in the garbage can as he went to answer the door. When he opened it he had to do a double take. The young man standing on his porch looked incredibly familiar, though he couldn’t quite place where he felt that he knew him from.

“Hi, I’m here for Addison?” The guy’s voice was higher than Dean expected, yet still deep. He wasn’t sure why he’d expected this guy to have a deep voice. Shaking off the bizarre sense of deja vu, he plastered on a smile and nodded, stepping aside to let him in.

“You must be Bill. I’m Addy’s father. She’s been expecting you.” It felt like a very “dad” thing to say and mentally Dean patted himself on the back for coming with that. Bill smiled nervously.

“It’s a pleasure to meet you, sir.” 

“Wow, manners. I like that.” Dean was mildly impressed.

“Oh, if my father heard I was ever rude to anyone, he’d be very upset. He raised me to always be respectful of everyone.” Bill was standing with his hands clasped behind his back, looking up at Dean with huge, blue eyes.

“Your father sounds like a wise man. I’ve raised Addy the same way.” 

Footsteps on the stairs drew both of their attention as Addison came down then. Her long chestnut brown hair, which was usually straight, had been curled at the ends and she was wearing the headband Dean had bought her last year for her seventeenth birthday, the one with the silver flower on the side. She looked beautiful.

“Ok, I’ll be back by ten, Dad. Love you.” She planted a kiss on Dean’s cheek before smiling at Bill and motioning for him to head to the door with her. Bill turned to face Dean once more.

“I’ll be a gentleman, I promise. I’ll have her home on time as well.”

Dean smiled. Yeah, this kid was alright. In a day and age where kids were lacking in respect for their parents, someone had worked hard to raise this boy to be a respectful, thoughtful human being.

“I appreciate that, Bill. You kids have fun now.”

Dean watched as they headed out to Bill’s car. Hell, the kid even opened the door for Addison! He really hoped it wasn’t all for show, just to impress him. As he closed the door he said a silent prayer that the kid really was that kind and thoughtful.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

“So, it’s just you and your dad?” Bill asked. They had just been given their menus and Addison was busy looking hers over, but she lifted her eyes to look at him.

“Yeah. My mom, she met someone when I was about three. Decided he was better than my dad and she left. They were never married. My dad wouldn’t let her take me because she had no intentions of letting him stay in my life, so instead she left me. She’s on her second husband now with four more kids. It’s just been my dad and me ever since.” 

“I’m sorry to hear that. What made you join the GSA? Are you just a supporter like me?” He was wondering about that. It had been a risk asking her out, not knowing if she even liked guys.

“Yep. My dad’s bi, and we got some flack over the years when he dated men. It tore apart a really good relationship he had with a guy I thought could end up being my stepdad, but my grandpa ruined that. It hurt me when they broke up because he really made my dad happy. It’s just been us ever since. For about six years now,” she replied.

“That’s sad. My dad got a lot of shit from his family too. His parents ostracized him, but my uncle and aunt always supported him. They still do. My dad has dated a little, but no one ever seemed to stand up to the standards of his high school crush. How you can love someone you never even talked to, I have no idea, but he swears the guy was perfect.” Bill sipped at the water that was brought, and the server took their order before leaving again.

“So…you don’t have a mom?” Addison was curious about that.

“My dad opted for surrogacy. My aunt carried me. My dad just knew he wanted kids. He got a donor egg from a friend and asked my aunt to carry, and voila, here I am,” Bill smirked. Addison laughed and shook her head.

“He must have been young. My dad was twenty two when I was born.”

“So was my dad, but he had already graduated college and was a published author by that time. He had two bestselling novels by the time he was twenty, six by the time he was twenty five, and he has forty novels written now. He’s working on another at the moment,” Bill said.

“Wow, I’m impressed. My dad had to work hard for everything he has. I remember him going to college after my mom left. Took him six years but he earned his teaching degree. He teaches first grade. I want to teach too. What do you want to do?” Addison asked.

“I was always told that I could be anything I wanted, and I am leaning towards medicine. I’d like to be a surgeon, like my uncle.” Bill replied.

“That’s so cool.” Addison gushed. Not only was Bill gorgeous, he was smart too. He was really going to score big points with her dad.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

Dean was kicked back on the couch when the front door opened and Addison walked in.

“Date go well?” he asked.

“Yes, it did. We went to dinner and then to play laser tag. Oh my God that’s fun! Aunt Charlie should go back with us. You too. It would be a blast,” she said as she dropped onto the seat next to him and leaned her head on his shoulder.

“That’s good. I’m glad you had fun. I haven’t played laser tag in ages. We should go. I’ll tell Charlie. You know her, she’s game.” He picked up the remote and changed the channel, finding a horror movie he hadn’t seen in a few years and settling on that.

“We talked a lot too. He wants to be a doctor. He already has a scholarship,” she said.

“Really? Wow. What school?”

“KSU. His first four years he wants to stay close to his dad. Then he’ll transfer.” She got up, flipping her hair behind her shoulders. “I’m going to change for bed and Skype Shayla. Night, Dad.”

“Goodnight, princess.” He tilted his head for the expected kiss she always planted on his cheek and as predicted, she gave him one. His eyes returned to the television screen. At least this kid had his head screwed on straight and knew what he wanted, he thought. Addison had good taste in guys.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

**OCTOBER**

“Dad, I’m going to Bill’s today. He’s introducing me to his dad, and we’re all going to go see a movie and then have dinner out. I won’t be home until tonight,” Addison said as Dean walked into the kitchen. He made a beeline for the coffee pot and poured himself a cup.

“That’s fine, I won’t be home today anyway. Your Uncle Sam asked me to come over to watch the game. I expect I’ll get home around ten or so. A bunch of the guys are coming over to watch with us.”

“Is Benny going to be there?” she asked.

Dean frowned around the lip of his mug. “I have no idea, and that ship sailed. He’s married, you know that.”

Addison sighed. “I know, Dad. I still miss him though.”

Dean’s expression relaxed and he walked over to her, reaching a hand out to smooth down a few stray strands of hair. “I know, sweetheart, and I’d be lying if I said I didn’t miss him too, but I messed that up and it can’t be fixed. We just have to move on.”

She wanted to argue that it wasn’t her dad that messed things up, it was Benny’s inability to handle the derogatory comments from her grandfather, John Winchester, but the man had died three years earlier, so really, there was nothing stopping her dad from finding someone new and being happy. This was a subject they had gone over so many times that now she felt like she was just beating a dead horse. Her dad believed he belonged alone, and that wasn’t fair to him. Sometimes he mentioned his first crush, the boy that changed everything for him, but not in a long time. It was back then that her dad had realized he was bi, but it wasn’t until he had graduated that he actually got involved with another man, a guy named Victor, and while it had been short lived, it settled the emotional battle Dean had been having in his head since the first moment he’d laid eyes on that boy his freshman year of high school, the one whose name was too painful for him to tell her. Dean liked men, and he liked them more than women. Still, he had ended up with Cassie, and he had loved her with everything he’d had. 

Addison knew how much her dad had loved her mom, and how utterly betrayed he’d been when four years into their relationship, when they were raising a happy, healthy three-year-old and had even been talking about giving her a sibling, she decided she no longer loved Dean and left him. It was a blur for her now but she remember that being one of the few times she’d ever seen her father cry. As little as she’d been and as confused as the entire situation had made her, she had tried to console him. The older she got and coming to realize what her mother had done to her father, it made her furious. Yes, she loved her mother and she knew her mother loved her, but her loyalty was to her father who had never done anything to hurt her or anyone else. If anything he had continued to persevere once her mother had left. 

Benny had come into their lives via Uncle Sam when Addison was four, but at first he and her dad had just been mutual acquaintances. She didn’t know the circumstances that brought them together, only that she had been thrilled to see her dad happy. They started dating when she was six and when she was seven, Benny moved in. For the first time in ages she’d felt like she had a family, and it felt complete. Benny would read to her at night when he tucked her in and cheer for her at her soccer games, as though he were her other dad, and God had she loved him like he was. She didn’t learn until later that the entire time her dad had been with Benny, her grandfather John Winchester had been doing everything he could to break them up. He called DCS, claiming Benny was sexually abusing Addison and while the charges were unfounded, it had caused a crack in the bond he had with her dad. Her grandfather had called Benny’s parents and outed him, he’d refused to allow him in his house, and had tried to fill her head with all sorts of terrible thoughts on same-sex relationships. Had it not been for her grandmother going against him and praising her father’s relationship and constantly telling Addison that the love her father and Benny had was beautiful and should be revered, not condemned, she wasn’t sure what her opinion would be now. 

Benny left after the sex abuse claim. He loved Addison like she was his own and didn’t want her getting hurt because of John’s ignorance. For the second time in her life she had to watch her father’s heart break. It was the second time she’d ever seen him cry. She’d been twelve when Benny left and while he and her dad remained friends, things were never the same between them. Two years ago Benny met a nice girl and last year they’d gotten married. She and her dad had attended the wedding. As much as she’d wanted to hate Andrea, she couldn’t. She was wonderful and treated Benny like he hung the moon and stars, and how could she hate someone that clearly adored the man she still looked at like he was other dad? They were expecting their first baby soon. That left her with a bittersweet feeling, like that should have been _her_ sibling. Standing here now, looking at her father, she could see the sadness he tried to hide. He still loved Benny, though perhaps he was no longer still in love with the man. And it hurt. She pulled him into a hug.

“It’s ok, Dad. I know there’s someone out there for you, someone you’re meant to spend the rest of your life with, and when you find them, you’ll know,” she whispered against his ear. He hugged her back, squeezing her a little tighter than usual. She knew he didn’t believe he’d ever find someone to spend the rest of his life with, but she had hope enough for them both.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

**DECEMBER**

Christmas was always a carefully done ballet in the Winchester family, and this year was no difference. Dean and Addison would join Sam and his family on Christmas Eve, along with their mother, Mary. Since John had died she spent more time with her sons and grandchildren, especially at the holidays. This year, though, they were doing things slightly different. Sam’s in laws were going on a cruise, a gift from Sam and Jess, so this year Dean and Addison were heading over to his mother’s house Christmas Eve, and Mary was going with Sam and his family on Christmas Day to Jess’ parents’ house. Christmas Day was usually when she would go spend time with her mother and siblings, except this year her mother was traveling out of state for the holidays. Being that she was now eighteen, Addison didn’t have to go if she didn’t want to. And she didn’t. She wanted to spend time with Bill. Still, she worried about her father, who would be sitting at home alone on Christmas drinking beer and wallowing in his misery. She brought this up to Bill over pizza one night as they sat in his room playing video games.

“Your dad’s not dating anyone?” Bill had asked.

“No, and he’s too proud to accept invitations from his friends. He thinks he’ll be imposing if he joins them,” she grumbled. Bill chuckled.

“Sounds like my own dad. He’s going to be alone on Christmas too. My Aunt Anna, she lives in Alaska, it’s where her husband is currently stationed. They spend time with her husband’s family every year, and my Uncle Gabe is covering shifts all week. He’s getting in the extra hours so he can take the time for the vacation he has planned at the first of the year for him and his wife. So dad’s going to be alone. He’s been a grump all month.” He paused for a moment, tilting his head as a thought came to him. “Say, it’s about time our parents met each other, right?”

She nodded slowly. “Yeah…”

“So, why don’t we treat our parents to dinner out? Introduce them and maybe they can be friends. It sucks to be alone at Christmas. At least they have us,” he said.

“So, we take them out for dinner on Christmas Day?” She really liked that idea.

He nodded. “Yeah. That way your dad’s not at home getting drunk and bemoaning his singleness, and my dad’s not angrily writing his bitter feelings into the next chapter of his book.”

“I like that idea. When I get home tonight I’ll tell my dad. I’ll make it sound like we’re doing this as a gift. He’s more likely to accept it as a gift than he is if he thinks we’re imposing on someone else’s holiday traditions.” She liked the idea of taking her dad out to dinner. Since getting her job at Hot Topic last month she had the money to do it, at least she did if Bill helped. Four people was a lot to have to pay for, and she’d sort of splurged on gifts for her dad this year.

“Yeah, my dad isn’t any better. He’s sort of socially awkward and avoids people because he doesn’t think they’ll like him, but he asks about you a lot. He likes you, says you were raised right because you’re so polite to him and respectful. I told him your dad’s a single father too and he did say your dad could always come over too if he was ever feeling too alone. So I think taking them both out and spoiling them for one night out of the year would be good.” Bill put the game on pause and looked over at her. “My dad’s downstairs, should be spring it on him now?”

“No, it’s still two weeks until Christmas. Let’s wait til a few days beforehand. Let’s find a nice restaurant that will be open and set up a reservation. My dad likes steak, what about yours?” she asked.

“Oh yeah, as health conscious as my dad might come off seeming to be, the man loves his steak and potatoes. I think I know just the place, and we’ll be able to afford it too.” He pulled out his phone and looked the place up.

“Cool.” She was excited. For once she would be getting the opportunity to spoil her father and show him how much he meant to her. To show him that no matter what, he wasn’t alone.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

“Dad…”

Dean slid his reading glasses off his nose and looked up at his daughter.

“Yes?”

“I am taking you out for dinner on Christmas Day,” she announced. He blinked in surprise.

“What about your mother? You’re supposed to spend the day with her and Todd.”

“Mom’s going with Todd to visit his grandparents this year. They’re not well enough to travel anymore, so they’re going to head out there instead. I don’t want to go to Vermont, especially at this time of year,” she replied.

“And you want to take me out for dinner? What about Bill?” he asked.

“Well, we got to talking and we want to spend Christmas together, but his dad is going to be alone for Christmas too, so we decided we’re taking you both out, so we’re all going to Rainer’s Steakhouse. We’ve already arranged for reservations. We’re not interrupting anyone’s celebrations. You’ll just be sitting here watching crappy television specials and drinking beer and his dad will just be at home moping and writing, and as much as we want to spend the day together, we also want to spend it with our dads, so this is our gift to you. Plus…we think it’s time for our parents to meet. I love him, Dad.” She sat down next to him at the kitchen table and when he looked into her eyes he saw that she was telling the truth. She really was in love with Bill. He placed a hand gently against her cheek.

“Alright, sweetheart. And thank you, it means a lot that you would want to take me out to dinner. I love you, princess.” 

She brought hand up to cover the one he had pressed against her cheek. “I love you too, Daddy.”

Tears pricked at the corners of his eyes at hearing her call him “daddy.” She hadn’t done that in years.

“So what should I wear? That’s a fancy place, isn’t it?” he asked before he could let his emotions take over.

“It’s not that fancy, but don’t worry, I bought you something nice to wear. It’s part of your gifts,” she replied.

He lowered his hand and smiled at his daughter. How had he created someone so beautiful? So perfect? He loved her more than anything in the world already, but it was moments like this that his love grew tenfold.

“Sounds good. What time are the reservations for?” he asked.

“Six. It’s going to be wonderful. You’ll get to meet Bill’s dad and see just where he gets his manners from. His dad is so nice. And guess what dad?”

He smiled at her excitement. “What?”

“The restaurant has _pie_.”

He grinned. “Well, Merry Christmas to me!”

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

Christmas Eve with the family was nice and it was the first year Dean didn’t have to label all of the gifts he’d bought for everyone from him and Addison, but he’d done so anyway, more out of habit than anything. Addison was proud to be able to hand gifts to everyone that she had bought, but most of all she was excited to give things to her cousins Anthony and Aubrey, her Uncle Sam and Aunt Jess’ twins. They were six, too young for gifts from her work where she got a discount, but she had still managed to find them gifts at a toy store in the mall and they were excited, throwing their arms around her neck and showering her with kisses as soon as they’d opened their presents. 

Part of her excitement was being able to buy for her father, who had given her everything and then some over the years. She loved seeing his eyes light up and the smile he gave with each new present she gave him, and seeing an excitement that surpassed his own when he saw the albums she had bought for him. He looked so young and innocent in that moment. She loved that. She had bought him a sweater to wear to dinner the following night, and it was a beautiful pale cream with flecks of brown and she smiled as she watched him run his fingers over the soft yarn.

“Thank you, princess.” He’d told her that after every present, but this one earned her a kiss on the cheek. Because it wasn’t just a sweater, it was a promise that he wasn’t alone, and that as far as she was concerned, he never would be.

The following day Dean slept in, but so did she. Around noon she headed over to Bill’s to open some more presents while Dean finished up some things around the house. He hung the new flannel shirts his brother had bought him along with the sweaters his mother had given him. The one from Addison was left out on his bed, and he chose a pair of black dress pants to wear with it. Sam had bought him a new Dremel set, and for a few hours he had fun playing with it. Addison returned, pulling him from his woodworking to shoo him off to take a shower. She investigated what he had chosen to wear with the sweater and while he was in the bathroom she chose a pair of shoes for him to wear and laid out the bracelet her Aunt Jess had bought him for Christmas. Before he came out of the bathroom she left to go pick out a dress to wear to dinner. The sweater and jeans she had worn over to Bill’s weren’t nice enough, in her opinion. After brushing her hair out and styling it up in plaits that she tucked a couple of silk rose hairpins into, she put on a dress she had bought a few months earlier, a cream, knee length piece with a black belt and scoop neck that was still this side of classy. It was cold and snowing but it was dry, not settling for long before it was blown around, so she felt confident that wearing her black heels would be alright. She was hoping she wouldn’t get snow in them.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

When Dean was finished shaving, dressing, and styling his own hair, he went to check on Addison. It was nearly five thirty. He knocked on her open bedroom door and popped his head in to see her sitting at her vanity, applying lipstick. She was a beautiful young lady, the perfect combination of both him and Cassie with smooth skin that leaned ever so slightly more towards her mother’s light caramel complexion, but with a light smattering of freckles across the bridge of her nose like he had. Her eyes were the same large, expressive hazel ones as Sam’s, and her hair was the same color as her uncle’s too, though she wore hers straight and long, all the way to her waist. Sam’s stopped just above his shoulders. She had Dean’s nose and lashes and when she smiled at him in the mirror, he couldn’t help but smile back. With makeup perfectly applied like this, he thought, and not for the first time, that she could be a model if she really wanted to be.

“You ready? We’ll want to start heading out now, so we’re not slowed down by idiot drivers,” he told her. She applied the last of the dark red lipstick to her lips before smacking them together.

“Yep, just let me grab my coat.”

She stood up and he nodded approvingly at her choice of dress.

“You look amazing, baby girl.”

“We match, Dad. Well, almost,” she said, grinning.

“I guess we do, huh.” He looked down at his own sweater, smiling. “I’ll grab my wallet, and we’ll get going.”

“Remember, Bill and I are paying!” She called after him.

“I know, but I still need my ID,” he called back.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

The restaurant was beautiful, nicer than Dean had expected. They walked in and his eyes were drawn up to the oak beams in the ceiling and the chandeliers that hung from them. For a moment he felt underdressed but as he looked around he saw that most of the men there were not wearing suits and ties, but varieties of button downs with blazers or sweaters like himself. A server approached them, a polite smile on his face.

“Do you have a reservation?” he asked.

“Yes, Robinson/Novak. Party of four,” Addison said. Dean cocked his head.

“Bill’s last name is Novak?” he asked as the server walked away to check on their reservation.

“Yup. Didn’t I tell you that?” 

“No. I used to go to school with some Novaks. Haven’t heard that name in years,” he said.

“I’m surprised you remembered at all. I don’t think I’ll remember half the names of the people I’m in school with even ten years from now,” Addison laughed. He chuckled.

“Well, the guy in high school that I had my first guy crush on? He was a Novak. Quiet, shy guy, but nice. I never could work up the nerve to talk to him though. Wish I had, he was beautiful.”

Addison looked at her dad’s far-away expression, knowing he was thinking back to that time in his life, before he’d had the guts to come out. She was infinitely proud of him for finding the inner strength necessary to not hide anymore.

“Your table is ready. The rest of your party is not here yet, though. Would you like to wait here or at the table for them?” The server was asking. Addison looked at all of the walk ins that were sitting and taking up all of the seating.

“We’ll wait at the table. I can’t stand for long in these shoes.” 

The server smiled and looked at her feet. “I imagine standing in those would get to be uncomfortable. I’ll take you to your table now.” He grabbed two menus and led them through the restaurant and around a half wall to a quiet little corner with only a few tables. He stopped at an empty one with four chairs. Addison sat down and Dean took the seat next to her. Bill could sit on the other side with his dad. He hoped the guy was as nice as Addison made him out to be or conversation would be awkward. At least they could talk about the kids, if nothing else. 

After being handed their menus and giving their drink orders: Coffee for Dean, a Coke for Addison, the server left and Addison launched into a conversation about the things Bill had bought her for Christmas, and what Bill’s father had bought her.

“His dad bought you something?” Dean asked, mildly surprised. Sure, he’d bought a small gift for his daughter’s boyfriend, but he hadn’t expected the boy’s dad to think the same way he did.

“Yep, see?” She had taken off her coat and held out her arm so he could see the silver charm bracelet hanging off it. He wished he’d brought his reading glasses so he could see it better, but from what he could see of it, there were three charms already on it, one for her birth sign (Scorpio), one for her favorite pastime (a musical note for her singing and involvement in choir), and what appeared to be a tiny apple.

“This is nice. Is this one an apple?” he asked.

“Yes. I told Bill’s dad that I wanted to be a teacher, like you, and he said that is a noble profession and that teachers don’t get nearly the respect they deserve, and so that’s to honor my decision to become one,” she explained.

“That’s really nice. Doesn’t really compare to what I got Bill though,” he said with a small laugh.

“What _did_ you get him?” she asked.

“Oh, you said he wanted to be a doctor, so I got him a book that Sam recommended, on anatomy. It was expensive as hell, but apparently it’s one that doctors rely heavily on, even after they’re finished with school and out working,” he replied.

“That’s wonderful, Dad. I think he’s really going to appreciate that.” She squeezed his hand and smiled at him.

“It’s in the car. We’ll give it to him later,” he said. She nodded in agreement.

“Hey!” Bill came around the corner and Addison looked up, smiling at her boyfriend. “Wow, you’re gorgeous!” he gushed, blushing when he heard Dean chuckle. She stood up to kiss him.

“Where’s your dad?” She asked.

“He’s having trouble finding parking so he told me to come in and find our table, in case you guys weren’t here yet,” he said as he sat down across from Addison. He looked at Dean and smiled politely. “Hello, Mr. Robinson.”

“Oh, name’s Winchester, not Robinson. Addy just has her mother’s maiden name,” Dean said.

“Oh, ok.” Bill nodded.

“Billy?” A deep gravelly voice called out from the other side of the half wall.

“Over here, Dad,” Bill called back. A man rounded the corner, his expression one of relief when he spotted his son. Dean felt a chill at the sound of the man’s voice and he turned in his seat to look up at him.

Holy

Fucking

Shit

The man caught Dean looking and turned to face him, his blue eyes widening in shock.

“ _Dean_?!”

Dean’s mouth opened and closed for a moment, but no sound came out at first. Finally he got a single word to form.

“ _Cas_?!”

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

 

“You guys know each other?” Bill asked as he looked between his father and Addison’s dad. When the men continued to stare at one another in shock he looked to his girlfriend for help. “Addison?”

She looked at him, running her tongue absently over her lower lip, forgetting that she was wearing lipstick as a thought formulated. _Oh_ …

“Mr. Novak, please, have a seat,” she said pleasantly. He must have heard her because he finally tore his eyes away from Dean and practically fell into the seat next to his son.

“So, I’m guessing this is one of the Novaks you went to school with, _right_ , Dad?” Addison elbowed her father in the side hard enough to jerk him out of his current stupor. 

“Uh, yeah, yeah, Cas and me, we went to school together. And his brother, Gabe,” he managed to stutter out. 

“Were you guys friends?” Bill asked. His father was unfolding the cloth napkin that his cutlery had been wrapped in and placing it neatly on his lap, deliberately not looking at Dean.

“Oh, no, we didn’t know one another, but I knew of Dean.” 

Dean watched Cas continue to smooth his hands over the napkin as he tried to appear nonchalant.

“Why didn’t you talk to me?” he suddenly asked. Cas looked up, blue eyes wide and cheeks tinged red. He seemed to be contemplating how to answer when a server appeared with Dean’s and Addison’s drinks. Bill and Cas both asked for unsweet tea, and the server was gone again.

“I was…shy back then. I really didn’t talk to anyone,” Cas said softly.

“Yeah, I talked to Charlie, that was about it,” Dean admitted. Cas glanced up, a soft smile on his lips. Dean was struck by how absolutely gorgeous the man was now compared to how he’d looked in high school. Time had done the man a world of good.

Oh right, and he was gay.

Holy shit, CAS WAS GAY.

The realization struck Dean as hard as if someone had just slapped him in the face. He took a deep breath and frowned down at his cup of coffee. When their fathers both fell silent Addison decided it was up to her to initiate conversation.

“So, did you graduate the same year?” she asked.

Dean glanced at her before nodding. “Yeah, Cas here was our valedictorian.”

“So was my Uncle Sam!” she said to Bill’s father. Cas looked at her and smiled.

“Yes, Sam Winchester was an exceptionally bright young man. Not that your father wasn’t too, because he was, you were-are...” His smile faltered and he suddenly looked horrified. Dean laughed.

“It’s ok, Cas, I know you weren’t insulting me.” He assured the other man. Cas’ expression relaxed and he gave a lopsided smile.

“Sorry, I don’t always say things the way I actually mean them.” 

“You’re not the only one,” Dean said, smiling. He was finally feeling himself relax a bit, though he was still in shock that the father of his daughter’s boyfriend was his high school crush. He took a sip of his coffee as the server returned with the iced tea. They gave their orders, and Cas smiled at Dean when he saw that they had ordered almost the exact same thing.

“So, um, what have you been up to since high school?” Cas asked him. Dean could hear how nervous he was. It was still endearing.

“What, Addison didn’t tell you?” he teased. Cas blushed, though he was smiling.

“No, she hasn’t told me much, otherwise I might have realized sooner that she was your daughter.”

“Ah. Well, I worked in my uncle’s garage for a while before I met Addy’s mom. When we split up I decided to take Sam’s advice, and I went to college. I now teach first grade, though next year I’m switching to third,” Dean replied. He glanced over to see his daughter watching him with a knowing expression. Damn it, Sam had really rubbed off on the kid.

“Oh, that’s wonderful. I believe she did mention that you teach, though I’m not sure if she told me you taught elementary.” Cas took a sip of his tea and looked briefly at his son, who had fallen into a conversation with Addison about some movie he wanted to take her to see.

“What about you, Cas? What have you been up to?” Dean knew the man was single and gay, and that excited him. He was trying to maintain his cool though.

“Oh, I write. I started my first book in high school, actually. I submitted it to like forty publishing houses before one finally took interest. It turned out to be a hit and I was signed to a five book deal. I went to college and double majored, earning two degrees, one in English and one in Creative Writing. After my second book was published I decided I wanted kids. I didn’t have much luck dating so my friend Meg offered to donate some of her eggs. I had money, I had a house, so I asked my sister to be the surrogate since she had already had a baby by that time, and she agreed. So by my twenty second birthday, I was a father. And yes, I know I was young, but then again I’ve always known what I wanted in life. I was emotionally ready for a child and Billy was absolutely perfect. Since then I’ve mostly just been writing, though I have done some teaching at the university. A creative writing course,” Cas’ voice was deeper than Dean remembered, and it sent shivers down his spine hearing it now. God, the man was sexy! He still had the messy, dark hair but the glasses were gone.

“Hey, what happened to your glasses?” Dean asked.

Cas blinked. Dean…remembered?

“Lasix. About five years ago. I got tired of contacts.”

Dean liked the glasses, but now he had an unobscured view of Cas’ bright blue eyes and he thought that was even better. “I might have to look into that. I’m now wearing reading glasses,” he chuckled. Cas smiled wider.

“Comes with getting older.”

Dean nodded. “Yes, it does.” He wondered what Addison had told Cas about him. Did Cas know he was bi? Could he possibly be interested? The way Cas was staring at him told him it was quite possible. But did he _know_?

“So, besides writing and raising a fantastic kid, what have you been up to?” he asked. He was hoping there would be an opening, some way to nonchalantly let Cas know he was definitely into men without having to openly flirt in front of their children.

Cas smoothed down the napkin in his lap absently again. “Oh, not much? Volunteering at a few food pantries, at the animal shelter near my house, that’s really about it. I…don’t have many friends. I still talk to Meg, and I have a few other friends I met through my brother. Occasionally I get invited over to my brother’s house to watch various sporting events.”

“I get the same invites from my brother,” Dean laughed.

“What about you, Dean? Addison didn’t mention any other family members. Is it just the two of you?” Cas asked.

There was the opening he needed, if he could just word it right.

“Yes. Her mother walked out on us when she was three. After that I concentrated on college for a while until I met my ex, Benny. We were together for about six years but my dad caused some problems for us and, uh, he left. That was six years ago. It’s just been us ever since.”

Nailed it, he thought smugly.

Cas was staring at him, his expression unreadable. 

“Mr. Novak, we need a speaker for the GSA meeting at the end of January. Do you think you could come and give your experiences?” Addison asked, cutting into his train of thought. He blinked and looked at her.

“You’re in the GSA as well?” He seemed surprised by that.

“Well…yeah. I’m a supporter, just like Bill. That’s how we met. Didn’t he tell you that? I support my dad,” she replied, giving her father a smile that he could see right through. Little shit was on to him.

“Oh.” Cas looked at Dean with wide eyes for a moment before looking at Addison again. “I would be honored, though I’ll admit, I don’t do very well in front of large crowds.”

“It’s thirty kids, give or take, but we’ve had a rise in bullying and attempted suicides lately. Kids need a morale boost, and to know that there is life after high school, and that things will get better. My dad already came in last year and talked to the kids. He has volunteered to come again in the spring since there are a lot of new faces, but we need some more people that are out and comfortable with themselves, to help spread hope,” she told him. Under the table she subtly patted her dad’s knee. Cas’ eyes swung back around to Dean.

“…You?”

Dean arched one eyebrow and smiled. “Me.” 

“I had no idea, back in high school,” Cas said, still soft spoken.

“I didn’t come out til I was long out of high school. Not til after Addy’s mom, actually,” Dean admitted. “My dad…he wasn’t supportive.”

“Nor were my own parents. I am only on speaking terms with my brother and sister. The irony is that my parents had the nerve to ask me for a loan a few years ago as they were close to being foreclosed upon,” Cas said with a snort and a shake of his head.

“Did you help them?” Dean asked.

“Would you have?” Cas countered. Dean thought for a moment. 

“Yes, I believe I would have.”

Cas smirked. “As would I have, but my brother stepped in and helped them before I could. Told them to never ask me for anything again. That if they couldn’t find it in their heart to accept me and love me as I am, then they have no right to ask for my help with anything. I still offered to help but my brother threatened to be the next to disown me if I did. I happen to love the idiot, so I refrained.”

“I understand where you’re coming from. It’s hard to deny your parents. They gave you life. I’d move heaven and earth for my mother. Maybe not for my dad though,” Dean said.

“Are you on speaking terms with him now?” Cas asked. Dean stared into his coffee cup for a moment before answering.

He, uh died, three years ago. And no, we were not on speaking terms when he died. I still harbored a lot of anger against him for everything he’d done to ruin my last relationship.”

“I’m sorry, Dean,” Cas said, and Dean could hear the genuine remorse in the man’s voice. There was nothing condescending in his tone at all. 

“It’s ok. I have a great family. Sammy’s a dad. Married with twins and a baby on the way.”

“What?! Aunt Jess is pregnant?!” Addison gasped.

“Yeah, but shhh, Grandma can’t know until the beginning of the second trimester. Your aunt is superstitious,” Dean told her.

“Oh my God! A new baby!” She clapped her hands excitedly. Cas was smiling at her and Dean was reminded again of what he had found so amazing about him all those years ago. There were no falsehoods with Cas. He wore his heart on his sleeve, and there had never been anyone more gentle. Cas was the boy that marched onto the football field in the middle of practice, in the pouring rain, when a squirrel was accidentally kicked by one of the players. He scooped it up in a box and took it to the nearest vet. It was all anyone could talk about at school the next day. Cas had been president of the horticulture club, the chess club, and for one year had even been on the LaCrosse team. Dean used to sit under the bleachers and watch him practice. Dean turned to look at his daughter.

“Just hush about it. And act excited when they finally make the announcement, ok?”

She nodded and excitedly began telling Bill everything she wanted to buy for the baby. Cas chuckled and turned his attention back to Dean.

“So, do you read, Dean?” he asked. Dean smiled.

“Yes, I do.”

 

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

From there they discussed books and television shows they both watched before moving on to discuss the people they still spoke to from high school. To Dean’s embarrassment it turned out that Cas knew Victor, but not well, and he knew one of Dean’s exes from high school, Lisa Braeden. Apparently she worked at the publishing house Cas worked with, though he rarely ever saw her. The food arrived and they chatted as they ate, the topic turning to food and then to Cas’ books. Dean was amazed that Cas had turned out to be such a prolific writer, though he’d never doubted that the man would end up doing some form of writing, not with the essays Cas used to write for their English class senior year, and the articles he wrote for the school newspaper.

“I honestly thought you’d have gone into journalism with how well written your articles for the school newspaper were.” Dean told him. Cas’ eyebrows rose hearing that. Dean had _read_ the school newspaper? No one read that thing!

“You actually read my articles?” he asked.

“I did. I kept them too, every single one of them, all four years,” Dean replied with a soft smile. He glanced over at their kids to see if they were listening but they were busy talking about an annoying coworker Addison had, oblivious to what their parents were talking about. Cas set his fork and knife down, his blue eyes searching Dean’s face, looking for a sign that what he was interpreting in the other man’s words were actually true.

“Why… _really_? You kept them?” He was so stunned by that revelation. Dean shrugged.

“They were important.” _You were important_ was what he really meant. For a long moment they just stared at one another over their half-finished meals. It wasn’t until they both realized the entire table had fallen silent and both Addison and Bill were watching them that they finally broke away.

“Am I maybe missing something here?” Bill asked, looking between the two men, who had both dug back into their food with way too much enthusiasm to be believable.

“My dad here had a huge crush on your dad in high school,” Addison told him. A half chewed piece of steak lodged in Dean’s throat when he gasped at his daughter’s words and he started coughing violently. Cas jumped up and knelt at his side.

“Daddy!” Addison cried. People from surrounding tables turned at the sound of her high pitched scream to look on in horror.

“Are you getting air?” Cas asked. Dean wheezed but nodded as he continued to cough.

Cas stood up and moved behind him, wrapping his arms around Dean and positioning his hands over his sternum. One good push and the piece of meat popped out, landing on the table.

“I’m sorry, Daddy! I didn’t mean to embarrass you and make you choke!” Addison had tears in her eyes and Dean, while still coughing, managed to give her an awkward pat on the back. 

“’S ok, baby girl.” His throat hurt and he winced. Cas returned to his seat and held out his glass of tea.

“This will burn less than coffee.” 

Dean gave him a weak smile before taking the glass and drinking some. It still hurt to swallow, but after a few more sips he felt a little better. It was nowhere near as bad as the time he had choked on a piece of too-dry leftover turkey when he was a kid. His mom had pulled him from his chair and done the Heimlich, sending the piece of meat flying across the table to bounce off his brother’s forehead. That had left him stuck eating Jello and soup for the next three days. This had barely been lodged in his throat so after finishing half the glass of tea, he felt much better and went back to eating.

“Thank you for that,” he said as he set the glass on the table. “And I’m sorry I drank half of your tea.”

Cas waved him off. “It’s perfectly fine.” He flagged down the waiter and ordered another tea for himself and one more for Dean.

Addison was leaning against her father, looking up at him with the same puppy dog expression her Uncle Sam always gave when they were kids, except she gave it better. 

“I’m alright, baby girl. Really. Finish your food.” He kissed her forehead and she smiled at him.

“Just don’t ever scare me like that again, ok?”

“I will try not to.” He winked at her and she snorted, rolling her eyes. Sometimes he thought she was more like Sam than she was like him. 

They all went back to eating though both of their kids were now watching Dean warily, as though they expected him to choke again. When he looked up he saw that Cas was watching him too.

“Is what she said true?” He finally asked once their kids had started up another conversation with one another.

Dean set his fork and knife down on his now empty plate and looked across the table at him. “Yeah, it was. All four years you were my biggest crush.”

Cas’ jaw fell a little at his confession. He glanced nervously at his son before looking at Dean again. It was really uncomfortable with their children as the audience.

“Can we talk about this some more after dessert?” His eyes were pleading with Dean to agree.

“Uh, sure.” Dean wasn’t sure if that was a good thing or not. Was Cas just embarrassed by Dean’s confession, or was he just too nice to tell him he’d never felt that way about him in front of their kids? Suddenly he felt absolutely stupid.

“If you’ll excuse me, I have to use the bathroom. Addy, if the server comes before I return, you know what kinds of pie I like.” Dean stood up quickly and left, hurrying towards the bathroom before he threw up everywhere.

“You should go after him,” Addison said to Cas. He snapped his head around to look at her.

“What?”

“You liked my dad back then, right? I mean, you’re still staring at him, so I’m guessing he was your epic high school crush too. He’s going to worry himself sick in there that you didn’t like him back. Don’t let him throw up the meal we’re paying a small fortune for,” she said.

“Was he the guy you mention all the time? The one you said you fell in love with but he never knew?” Bill asked his father. Cas’ cheeks were burning as he got to his feet, tossing his napkin over his plate.

“Yes, now if you’ll excuse me.” He hurried off in the direction Dean had gone.

“You know, the chances that we’d meet and fall in love, and that our dads had such huge crushes on each other in high school are like so astronomical. I think fate really intervened here,” Addison mused.

“Well, neither of them ever left their hometown. It was inevitable that at some point their paths would cross, though this wasn’t how I pictured it. I’m just glad they’re getting the chance to actually tell one another how they felt back then. My dad is, for lack of a better word: pathetic,” Bill said. Addison tapped his hand.

“Don’t call your dad pathetic; he’s sweet and adorable. He can’t help it that he has social anxiety. My dad’s just an introvert by choice. But he has always thought fondly of your dad. Never told me his name though. Until today when I gave the name on the reservation. He mentioned that he’d gone to school with a couple of Novak kids, and then the look he gave your dad and the fact that they knew who each other were? Yeah, I put one and one together. I met your Uncle Gabe and there’s no way my dad would have ever had a crush on him.” 

Bill snorted. “I don’t know how my aunt Kay even tolerates him, seriously. He’s so obnoxious.”

“Hey, she likes that,” she shrugged. He leaned across the table and kissed her.

“And I like you.”

“Just like?” she asked, arching one brow at him. He grinned and leaned in to kiss her again.

“My mistake. _I love you_.”

She smiled back at him. “I love you too.”

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

“Dean?” Cas pushed open the bathroom door and stepped in.

“Go away,” Dean said from one of the stalls.

“I will not go away. Open the door.” Cas peeked under each door until he found the one Dean was sitting in.

“No,” Dean muttered.

“You know, this is very high school of you. We’re both rational adults here. Please open the door before I am forced to stoop to your level and crawl underneath it to join you. I rather like my pants without urine and feces on them.” Cas crossed his arms and waited. A few seconds later the lock clicked and the door swung open a few inches, though Dean did not come out. He pushed the door open a bit to see Dean sitting on the closed toilet lid with his elbows on his knees and his head in his hands.

“Dean,” he said softly and reached out to touch the other man’s hand. Dean lifted his head, looking up at him in confusion.

“It’s been twenty two years,” Cas said.

“Since we graduated? Yeah, don’t remind me.” Dean went to drop his hands but Cas grabbed the one he’d been touching.

“No, that’s not what I’m referring to. It’s been twenty two years since I last saw you, and everything I felt then, it all came rushing back the moment I saw you tonight. I just couldn’t say something like that in front of my son. He has a tendency to tease me, and I don’t handle that well. Dean, I was crazy about you in high school, but I was scared. Kansas isn’t exactly the best state in which to be gay, especially not back when we were kids. I wanted to tell you, but I was so afraid you’d make fun of me, or that other people would bully me worse than I already was, and…I was just scared. So scared you’d reject me, that you wouldn’t feel the same way.” Cas poured his heart out, figuring it was time to let the cards fall where they may. Dean stood up and Cas was forced back a few steps in the cramped space.

“You’re telling me you felt the same way?” Dean’s heart was racing, leaping into his throat when Cas nodded.

“And…now? How do you feel now?” 

Cas smiled shyly up at him. “Like I’m back in high school with the most gorgeous boy in the entire school.”

Dean let out a tight laugh and shook his head. “Cas, you were the gorgeous one. You still are.”

Cas’ expression was one of amused skepticism, as though maybe he thought Dean was on something. “I would have to disagree.”

Dean took a step closer. One more and he’d be chest to chest with the boy who had managed to steal his heart all those years ago without ever having said a single word to him.

“I would like the chance to take you out, like I wanted to all those years ago. What are you doing tomorrow for dinner?” he asked. Cas smiled so wide Dean could see every tooth in his mouth. It was a glorious sight to behold. 

“I would love to go to dinner with you. I’m free tomorrow night. Now, can I ask you a question?”

“Sure, anything.” Dean said.

“Can you please kiss me? I spent so many nights dreaming of what it would be like to kiss you. I’m still dying to know.”

This time Dean did move closer, crowding Cas up against the closed stall door. Tangling one hand in Cas’ hair he pulled him in, kissing him the way he’d dreamt of doing all those years ago. Cas let out what sounded like a contented sigh, kissing him back just as eagerly.

“I feel like a kid whose dreams are finally coming true.” Dean leaned his forehead against Cas’ and smiled. Cas smiled right back.

“For me, Dean, they truly are.” He’d never said truer words in his life.

**Author's Note:**

> So? Did you like it? Leave me a comment and a kudos, let me know! Thank you for reading.


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